Aug. 12, 2025

Sales Isn’t a Math Problem It’s Psychology with Benjamin Dennehy

Sales Isn’t a Math Problem It’s Psychology with Benjamin Dennehy

This episode is a punch in the face to every sales myth you’ve ever believed. Caleb sits down with Benjamin Dennehy, famously branded the UK’s Most Hated Sales Trainer, to dismantle the fake confidence, emotional attachment, and lack of process plaguing modern sales teams. If you want to stop losing deals—and your dignity—this one’s a must-listen.


Benjamin goes deep into the psychology of selling, why being liked is killing your close rate, and how most entrepreneurs unknowingly train their teams to be manipulated by buyers. Brutal honesty meets elite strategy in this hilarious, no-holds-barred conversation.


TAKEAWAYS

  • Most salespeople are emotionally attached to outcomes—and it’s killing their performance.
  • Your prospects are following a process designed to deceive and plunder you.
  • If you don't control the sales process, you’re being controlled by it.
  • Order takers aren’t salespeople. Learn the difference or lose money.
  • Sales must be structured, controlled, and disqualifying—not winged.


RESOURCES MENTIONED

Benjamin Dennehy Official Site


FOLLOWS

⁠⁠Oak IQ Investments⁠⁠

⁠Own The Exit⁠

⁠Caleb Investing⁠

Benjamin Dennehy


CHAPTERS

1:24 Why He Calls Himself “Most Hated”

5:06 Emotional Weakness in Sales

9:43 Why Most Hires Are Sales Fails

14:35 Sales Isn’t a Numbers Game

21:29 The Prospect Matrix Exposed

30:02 How to Sell Without Being Used

37:14 Proof His System Actually Works

45:09 His Wild Exit Strategy

48:07 Benjamin’s One Big Lesson

51:08 Free Gift for Listeners


KEYWORDS

sales training, sales psychology, emotional selling, sales process, disqualifying prospects, high ticket sales, sales team management, Benjamin Dennehy, own the exit podcast, how to close deals, sales strategy, sales mindset, sales objections, elite sales tactics, business to business sales


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